NP-MRD: Showing NP-Card for {2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate (NP0148455)

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Record Information

Version

1.0

Created at

2022-09-02 04:12:22 UTC

Updated at

2022-09-02 04:12:22 UTC

NP-MRD ID

NP0148455

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate

Description

{2,6,6,14,19-Pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]Henicosa-4,10-dien-11-yl}methyl acetate belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. {2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate is found in Talaromyces amestolkiae. It was first documented in 2022 (PMID: 36049892). Based on a literature review a significant number of articles have been published on {2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]Henicosa-4,10-dien-11-yl}methyl acetate (PMID: 36049891) (PMID: 36049888) (PMID: 36049887) (PMID: 36049886).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206122D          

 35 39  0  0  0  0            999 V2000
    4.5850   -2.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994   -2.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3226   -0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0879    0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022206122D          

 35 39  0  0  0  0            999 V2000
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 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 35  1  0  0  0  0
 23 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0148455

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC2OC(=O)C3(C)CC4C(COC(C)=O)=C5CC(=O)OC(C)(C)C5=CC(=O)C4(C)C(C23)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O9/c1-11-21(30)19-20-22(33-11)34-23(31)25(20,5)9-16-14(10-32-12(2)27)13-7-18(29)35-24(3,4)15(13)8-17(28)26(16,19)6/h8,11,16,19-20,22H,7,9-10H2,1-6H3

> <INCHI_KEY>
MZYSDGMJSZVIFW-UHFFFAOYSA-N

> <FORMULA>
C26H30O9

> <MOLECULAR_WEIGHT>
486.517

> <EXACT_MASS>
486.188982546

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.75097531784341

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosa-4,10-dien-11-yl}methyl acetate

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
1.8342517760000008

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.474126182796052

> <JCHEM_PKA_STRONGEST_BASIC>
-4.386133684518075

> <JCHEM_POLAR_SURFACE_AREA>
122.27000000000001

> <JCHEM_REFRACTIVITY>
120.67139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosa-4,10-dien-11-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.559  -4.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.279  -4.091   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.897  -4.771   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.380  -2.554   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.100  -1.698   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.202  -0.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.631   0.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.688  -0.705   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.186  -0.350   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.244  -1.469   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.627   1.126   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.570   2.245   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.856   3.092   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.959   3.659   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.072   1.890   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.193   3.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.656   3.256   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.081   4.685   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.619   2.118   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.263   3.616   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.862   0.597   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.666  -0.373   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.228   0.177   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.310  -1.361   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.857  -0.524   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.618  -2.045   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.234   0.563   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.464   1.936   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.090   3.373   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.878   4.572   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.324   6.009   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.399   4.333   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.323   5.564   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.181   2.668   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.985   1.697   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   34                                             
CONECT   20   19                                                            
CONECT   21   19    6   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   35                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   19   35                                                  
CONECT   35   34   28   23                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
{2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0,.0,.0,]henicosa-4,10-dien-11-yl}methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₀O₉

Average Mass

486.5170 Da

Monoisotopic Mass

486.18898 Da

IUPAC Name

{2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosa-4,10-dien-11-yl}methyl acetate

Traditional Name

{2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosa-4,10-dien-11-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC1OC2OC(=O)C3(C)CC4C(COC(C)=O)=C5CC(=O)OC(C)(C)C5=CC(=O)C4(C)C(C23)C1=O

InChI Identifier

InChI=1S/C26H30O9/c1-11-21(30)19-20-22(33-11)34-23(31)25(20,5)9-16-14(10-32-12(2)27)13-7-18(29)35-24(3,4)15(13)8-17(28)26(16,19)6/h8,11,16,19-20,22H,7,9-10H2,1-6H3

InChI Key

MZYSDGMJSZVIFW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Talaromyces amestolkiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Furopyran
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Gamma butyrolactone
Tetrahydrofuran
Furan
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.42	ALOGPS
logP	1.83	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	122.27 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	120.67 m³·mol⁻¹	ChemAxon
Polarizability	48.75 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163049814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiang R, Li M, Gu Z, Liu H, Zeng H, Peng J: Chronic endometritis positively correlates with the aggravation of intrauterine adhesions but has limited effects on reproductive prognosis with antibiotic application. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14434. [PubMed:36049892 ]
Li M, Yue C: Abnormal uterine artery Doppler ultrasound during gestational 21-23 weeks associated with preeclampsia. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14435. [PubMed:36049891 ]
Meyer R, Weisz B, Eilenberg R, Tsadok MA, Uziel M, Sivan E, Mazaki-Tovi S, Tsur A: Utilizing Machine Learning to Predict Unplanned Cesarean Delivery. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14433. [PubMed:36049888 ]
Crockett C, Lorimer C: OncoFlash - Research Updates in a Flash! (September Edition). Clin Oncol (R Coll Radiol). 2022 Sep;34(9):551-553. doi: 10.1016/j.clon.2022.07.009. [PubMed:36049887 ]
Authors unspecified: Corrigendum. Low Urin Tract Symptoms. 2022 Sep;14(5):405. doi: 10.1111/luts.12458. [PubMed:36049886 ]
LOTUS database [Link]

Showing NP-Card for {2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate (NP0148455)

MOL for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

3D MOL for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

3D SDF for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

3D-SDF for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

PDB for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

3D PDB for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

SMILES for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

INCHI for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

Structure for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)

3D Structure for NP0148455 ({2,6,6,14,19-pentamethyl-3,8,15,20-tetraoxo-7,16,18-trioxapentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosa-4,10-dien-11-yl}methyl acetate)